Find hotels in Pittsfield, IL from CA $89

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Top 10 Pittsfield hotels and places to stay

Rodeway Inn

2.0 star property
6.8 out of 10, (111)
"This motel is more than 70 years old. The owners have made significant upgrades to a very old motel. Room looks nice upon entry and it was impeccably clean. The bed was possibly the best i have encountered in years. What you cant change are 2 foot by 2 foot showers, and a lack of heating controls during the cold months. It's an old central baseboard heating system for the whole operation. Staff was helpful and pleasant. This motel is a good budget option, but its still very old."
The price is CA $89
CA $98 total
includes taxes & fees
Dec 29 - Dec 30
Rodeway Inn

Monroe Street Suites

2.5 star property
9.6 out of 10, Exceptional, (52)
"Loved the place! Super cute! Will stay there again! "
The price is CA $107
CA $118 total
includes taxes & fees
Jan 23 - Jan 24, 2025
Monroe Street Suites

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (120)
"Great place to stay!"
The price is CA $171
CA $188 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Green Acres Hotel

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (313)
"Very comfortable, home, atmosphere. The staff was great!!!! Couldn’t ask for a better place to stay!"
The price is CA $157
CA $173 total
includes taxes & fees
Jan 25 - Jan 26, 2025
William Watson Hotel

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is CA $320
CA $457 total
includes taxes & fees
Jan 23 - Jan 24, 2025
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (71)
"Thanks for having us"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (50)
"We stayed a few nights. House is clean and in very good shape. People are very nice and easy to work with."
The price is CA $280
CA $318 total
includes taxes & fees
Dec 26 - Dec 27
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Newly Remodeled Town House!

9.4 out of 10, Exceptional, (6)
"Traveled to the area for a wedding, and this home was just what we needed for two nights. It looks like they’re adding to the place to make it more homey. It was my husband and I with our four daughters. Having one bathroom was a challenge, but doable. The beds were comfy. It was very clean and quiet."
The price is CA $151
CA $297 total
includes taxes & fees
Jan 25 - Jan 26, 2025
Newly Remodeled Town House!

Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake.

The price is CA $308
CA $437 total
includes taxes & fees
Jan 25 - Jan 26, 2025
Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake.

Buckhorn Barndo Nature Retreat-near Siloamsprings

2.0 star property
Buckhorn Barndo Nature Retreat-near Siloamsprings

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (4)
"It was a delightful stay - games on the patio, corn hole on the desk, swimming, fishing, walks, and sitting around the fire. Also, we greatly appreciated the ample fridge and freezer space."
Idyllic Mt Sterling Retreat w/ Private Lake!

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!

Upgraded farmhouse between Springfield Illinois and St.Lous Missouri

4.0 out of 10, (1)
"Host double booked over me for his “private” hunting business. Couldn’t use living room or kitchen because his other guests had all their hunting gear in them. My bed collapsed the second day. Real nightmare. I would never recommend this property to anyone. "
Upgraded farmhouse between Springfield Illinois and St.Lous Missouri
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Where is the best place for a stay in Pittsfield?

Monroe Street Suites is a favorite property for Expedia customers. This hotel offers free parking and free WiFi. Traveler reviews also recommend William Watson Hotel and Green Acres Hotel as top choices for your stay. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental that Pittsfield has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This Pittsfield vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, you'll find most room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

For more information about picking new dates or cancelling your trip to Pittsfield, click here.

What's the best budget-friendly hotel in Pittsfield?

Based on reviews, William Watson Hotel is a popular 3-star property for our travelers looking for an economical choice, and features free on-the-go breakfast and free WiFi. View all budget hotels in Pittsfield.

What's the best accommodation for families in Pittsfield?

Rodeway Inn is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Other good options for your kid-friendly vacation include Monroe Street Suites and Green Acres Hotel. Find more child-friendly accommodations in Pittsfield.

What is the favorite LGBTQ-friendly hotel in Pittsfield?

William Watson Hotel is a top LGBTQ-friendly hotel that features free breakfast and free parking. See all available hotels listed as LGBTQ-friendly in Pittsfield.

What's the best pet-friendly place to stay in Pittsfield?

Rodeway Inn is a top hotel for people traveling with their pets, and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

Where is the best hotel to stay near Old Orchard Country Club?

Green Acres Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located 2.4 mi (3.9 km) from Old Orchard Country Club. Other good choices within 5 miles include William Watson Hotel and Monroe Street Suites.

What's the best boutique-style hotel in Pittsfield?

William Watson Hotel is a favorite 3-star hotel with our travelers looking for a stylish accommodation, featuring 14 guestrooms, free parking, and free WiFi. See all boutique hotels in Pittsfield.

What are some accommodations with pools in Pittsfield?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Features sun loungers, an outdoor pool, and complimentary wireless internet access. View all hotels with pools in Pittsfield.

How is it to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer including the cafes, entertainment choices, and breweries. Tourists can also enjoy so much more including its theaters. In Pittsfield, there are 10 hotels and other accommodations to choose from. Find out more about Pittsfield.

What is there to see in Pittsfield?

Cultural venues include Pike County Historic Museum and John Greene Shastid House. A couple of additional sights to add to your agenda are Old Orchard Country Club and King Park. Check out what more to see and do in Expedia's Pittsfield guide.

What's the weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Pittsfield is 46 inches.